Patent GB-498136-A (GB)
Title: Manufacture of amide-like condensation products
Filed: 1937-06-30
Abstract: Amide-like condensation products are manufactured by causing an aminocarboxylic acid or a water-soluble salt thereof to react in the presence of an agent having an alkaline reaction with the halide of a carboxylic acid of the general formula R.X.R1.COOH, where R is an aromatic ring system substituted at least once by an aliphatic hydrocarbon radicle of at least 8 carbon atoms, R1 is an aliphatic hydrocarbon radicle, the chain of which may be interrupted by oxygen, and X is O or S. Solutions of the alkali metal or ammonium salts of the products, or their salts with organic bases, may be employed as wetting, dispersing, emulsifying or purifying agents.  The free acids or their salts may be used in conjunction with organic solvents, with fatty acids, with carboxylic acids formed by oxidizing paraffin, or with water-soluble salts thereof, with soap substitutes or other textile adjuvants, with sodium carbonate, sodium pyrophosphate or other phosphates or with other products having a similar action on the salts causing hardness in water, or with bleaching agents.  In examples: (1) the sodium salt of sarcosine is heated in aqueous solution with p-iso-tetradecylphenoxyacetyl chloride with the addition of caustic soda; the product is a washing agent; (2) octyl-1-naphthoxyacetyl chloride (corresponding to the acid obtainable as described in Specification 490,416) dissolved in carbon tetrachloride is added gradually to a warm aqueous solution of the sodium salt of sarcosine, with the addition of caustic soda; (3) p-iso-dodecylphenoxyacetyl chloride is stirred with an aqueous solution of sodium iminodiacetate with the addition of caustic soda; (4) a solution of p-iso-dodecylphenoxyacetyl chloride in carbon tetrachloride is introduced into a warm aqueous solution of sodium p-aminobenzoate, with the addition of caustic soda; (5) p-octylphenoxyethoxyacetyl chloride is heated with an aqueous solution of the sodium salt of sarcosine with the addition of a commercial mixture of mono-, di- and triethanolamine; (6) p-iso-dodecylphenylthioglycollic and chloride is heated with an aqueous solution of sodium aminoacetate, the solution being kept alkaline.  Other starting materials specified are, on the one hand, aminopropionic acid, aminobutyric acid, a -methylaminolauric acid, aminoacid mixtures such as are present in the different stages of decomposition of natural albuminous substances such as wool, silk, horn or leather, aminophenoxyacetic acids and aminosalicylic acids, and, on the other hand, the halides of iso-octylxylene-hydroxypropionic acids, isotetradecylphenoxy-a -butyric acids, iso-octylphenoxyethoxyacetic acids and dodecylphenylpentaglycol ether acetic acids.  The Provisional Specification comprises the use, as starting materials, of carboxylic acids, preferably in the form of a halide, having the general formula A-R, where A is an isocyclic (aromatic or hydroaromatic) ring system substituted p  at least once by a hydrocarbon radicle having at least four carbon atoms and R is a COOH group or a hydrocarbon radicle carrying a COOH group and having a carbon chain which may be interrupted by hetero-atoms and which is linked to A directly or through a hetero-atom.  In additional examples: (a) iso-octyltoluic acid chloride is introduced into a solution of sodium aminoacetate, with the addition of caustic soda; (b) dodecylphenylpropionyl chloride is similarly reacted with sodium iminodiacetate.  Other additional starting materials specified are iso-butylbenzoic acid, diiso-butylbenzoic acid, hexylbenzoic acid, dodecylxylic acid, iso-tetradecylnaphthoic acid, octodecylhexahydrobenzoic acid, iso-octylsalicylic acid, isobutylphenoxyacetic acid,iso-hexylcresoxyacetic acids, dibutylnaphthoxyacetic acids, iso-dodecylhexahydrophenoxyacetic acid, p-cyclohexylphenoxy-a -lauric acid, o- and p-benzylphenoxypropionic acid, p-phenylphenoxyacetic acid, the hydrogenation products of these acids, iso-octylphenylglycine, iso-heptylphenylmercaptoacetic acid, tributyl phenylacetic acid, iso-octylphenylhydrocinnamic acid, butylphenylbutyric acid, dodecylbenzoylpropionic acid and cyclohexylbenzoylbenzoic acid.